Record Information |
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Version | 2.0 |
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Created at | 2021-06-21 00:44:10 UTC |
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Updated at | 2021-06-30 00:18:53 UTC |
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NP-MRD ID | NP0043284 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | withawrightolide |
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Provided By | JEOL Database |
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Description | (1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0²,⁷.0⁵,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]Nonan-3-one belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. withawrightolide is found in Datura wrightii. It was first documented in 2013 (Zhang, H., et al.). Based on a literature review very few articles have been published on (1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0²,⁷.0⁵,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]Nonan-3-one. |
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Structure | [H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]4([H])C([H])([H])O[C@]5(C(=C([H])[H])C(=O)O[C@]4([H])C5([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@]2(C(=O)C([H])([H])[C@]3([H])C([H])([H])[C@]123)C([H])([H])[H] InChI=1S/C28H38O5/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23(30)28-11-15(28)9-22(29)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,30H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19-,20+,21-,23-,25+,26-,27+,28+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C28H38O5 |
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Average Mass | 454.6070 Da |
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Monoisotopic Mass | 454.27192 Da |
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IUPAC Name | (1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one |
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Traditional Name | (1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]4([H])C([H])([H])O[C@]5(C(=C([H])[H])C(=O)O[C@]4([H])C5([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@]2(C(=O)C([H])([H])[C@]3([H])C([H])([H])[C@]123)C([H])([H])[H] |
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InChI Identifier | InChI=1S/C28H38O5/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23(30)28-11-15(28)9-22(29)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,30H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19-,20+,21-,23-,25+,26-,27+,28+/m1/s1 |
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InChI Key | RWZUJIPMFKTTKN-BLMPNAGISA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Datura wrightii | JEOL database | - Zhang, H., et al, J. Nat. Prod. 76, 445 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Steroid lactones |
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Alternative Parents | |
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Substituents | - Steroid lactone
- Androstane-skeleton
- Delta valerolactone
- Delta_valerolactone
- Oxane
- Cyclic alcohol
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Lactone
- Organoheterocyclic compound
- Carboxylic acid derivative
- Oxacycle
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Alcohol
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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